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Chemical Structure| 661-19-8 Chemical Structure| 661-19-8
Chemical Structure| 661-19-8

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CAS No.: 661-19-8

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1-Docosanol is an inhibitor of lipid-enveloped viruses which can inhibit replication of herpes simplex virus and respiratory syncytial virus.

Synonyms: Behenyl alcohol; n-Docosanol; Nacol-22-97

4.5 *For Research Use Only !

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Product Details of 1-Docosanol

CAS No. :661-19-8
Formula : C22H46O
M.W : 326.60
SMILES Code : CCCCCCCCCCCCCCCCCCCCCCO
Synonyms :
Behenyl alcohol; n-Docosanol; Nacol-22-97
MDL No. :MFCD00002939
InChI Key :NOPFSRXAKWQILS-UHFFFAOYSA-N
Pubchem ID :12620

Safety of 1-Docosanol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of 1-Docosanol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 661-19-8 ]

[ 661-19-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6608-47-5 ]
  • [ 661-19-8 ]
  • [ 75391-27-4 ]
  • 2
  • [ 661-19-8 ]
  • [ 3543-75-7 ]
  • [ 1609623-09-7 ]
YieldReaction ConditionsOperation in experiment
43.1% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; Preparation of 4-{5-[Bis-(chloroethyl)-amino]-l-methyl-lH-benzimidazol-2-yl}butyric acid docosyl ester (<strong>[3543-75-7]bendamustine</strong> C22 ester): A 250 mL three necked round bottom flask equipped with a stir bar, thermocouple and nitrogen in/outlet was charged with 5.0 g (12.7 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 4.2 g (12.9 mmol, 1.01 eq) of teradecyl alcohol, 2.7 g (12.9 mmol, 1.01 eq) of dicyclohexyl carbodiimide (DCC), 50 mL of dichloromethane (MDC) and 0.16 g (1.27 mmol, 0.1 eq) of Nu,Nu-dimethylamino pyridine (DMAP). The reaction mixture was stirred at room temperature overnight at which time an HPLC analysis indicated the reaction was complete. Solids were removed by vacuum filtration and the wetcake was washed with 50 mL. Two alternate purification procedures were developed. The filtrate was washed with DI water (2 X 150 mL), dired over sodium sulfate, filtered and concentrated to dryness in vacuo. The resultant waxy residue was chromatographed on 80 g of silica gel 60, 230-400 mesh eluting with a gradient beginning with 100% MDC, then 0.5% methanol/MDC and finally 1% methanol/MDC collecting 100-150 mL fractions. Fractions containing the desired product were combined and concentrated to dryness in vacuo. The residue was again triturated with 20 mL of MDC and the undesired solids removed by filtration. The filtrate was concentrated in vacuo to yield 3.65 g (5.5 mmol, 43.1%) of the desired product as a waxy white solid with a purity of 95.7A%. NMR (400 MHz, CDC13) delta 7.17 (d, J= 8.72 Hz, 1H), 7.08 (d, J= 2.28 Hz, 1H), 6.78 (dd, J= 2.36, 8.72 Hz, 1H), 4.05 (t, J= 6.76 Hz, 2 H), 3.72 (m, 4H), 3.70 (s, 3H), 3.63 (m, 4H), 2.91 (t, J= 7.44 Hz, 2H), 2.49 (t, J= 7.08 Hz, 2H), 2.18 (m, 2H), 1.60 (m, 2H), 1.32 (m, 38H), 0.88 (t, J= 6.64 Hz, 3H).
 

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